


Underneath

by ObsidianRomance



Series: Drunk!Dean 'verse [7]
Category: Supernatural
Genre: Anal Fingering, Anal Sex, Barebacking, Bottom Dean, But it's not very good, Drunk Dean, Established Relationship, M/M, Panties, Stripping, Top Sam
Language: English
Status: Completed
Published: 2014-08-02
Updated: 2014-08-02
Packaged: 2018-02-11 11:30:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,625
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2066508
Author URL: https://archiveofourown.org/users/ObsidianRomance/pseuds/ObsidianRomance
Summary: <blockquote class="userstuff">
              <p>Dean gets it into his crazy head that he is going to treat Sam to a striptease. Thankfully he's better at taking his brother's dick than he is at stripping.</p>
            </blockquote>





	Underneath

**Author's Note:**

> **Disclaimer** : I do not own these characters.  I am just using them for fun. Also, the song I am using belongs to Warrent. You probably all know "Cherry Pie" but I just want to make everyone know that I DON'T OWN THE SONG. Just using it for funny moments.  
>  **Beta** : The ever lovely [](http://demondetox.livejournal.com/profile)[](http://demondetox.livejournal.com/)**demondetox**.My poor wifey was so sick and still beta'd. I love her. **  
> **  
> Author’s Note: Happy Birthday to[](http://kinkajou.livejournal.com/profile)[ **kinkajou**](http://kinkajou.livejournal.com/)! I am posting the last planned work in The Misadventures of Drunk Dean. (List of Drunk!Dean: [Stealthily Oblivious](http://obsidianromance.livejournal.com/72266.html), [Finding Fault](http://obsidianromance.livejournal.com/70942.html),[ It's Going To Be A Long Night](http://obsidianromance.livejournal.com/72825.html), [Making Good On Promises](http://obsidianromance.livejournal.com/71510.html), [Down and Dirty](http://obsidianromance.livejournal.com/71321.html) and [Sore Winner](http://obsidianromance.livejournal.com/87093.html)). I hope you enjoyed my drunk and horny Dean. I am not done playing wit him. He is kind of fun. So I am sure he will pop up every now and then.

Dean has an idea. It’s a pretty good idea, he thinks, but it keeps getting better the more he drinks. He’s not trying to get fall down drunk or anything but there are nerves in his belly and he keeps refilling his glass of whiskey over and over _and over_ again.

He figures it’s helping because now his plan is genius.

Everything is good to go. All he has to do is wait for Sam to return from… _whatever it is he said he was going to do_ …and put things into action. It’s mildly troublesome that he can’t remember exactly what Sam is off doing but he figures that’s his own fault because his brain had tuned Sam out in favor of focusing on tonight’s plan. He’s sure it’s something important like groundwork for a case or something. Dean had made up some excuse that he needed to do some of his own research, but other than throwing him a confused eyebrow raise, Sam left him to it.

And the more he thinks about it, the more Dean is certain that what he’s up to is pivotal to any other steps of their casework. The most important, in fact. Sometimes he and Sam forget that they are just two men who need to take a step back so they can refocus, making them all the stronger.

So now he gets to wait because Sam sure is taking his sweet ass time and Dean’s got little else to do but knock back another whiskey. And _maybe_ Dean’s getting drunker than he originally planned but he can handle that. He’s pulled off plenty of things while thoroughly shitfaced.

The door to the motel room pushes open and Sam immediately launches into speech, which is not at all what Dean feels like spending time on. Smirking, he gets to his feet and makes a straight shoot for Sam.

“So, I think it’s safe to say we – ” Sam finally looks up, just in time to brace himself for Dean’s weight. His eyes go wide when the man launches them into a kiss and he has to bring his hands up to bracket Dean’s arms and hold him steady. “Whoa, hey,” Sam breathes out but doesn’t get much else in because Dean’s tongue is in his mouth and he’s left to deduce what’s going on.

Pressing more of his weight into Sam’s form, Dean pushes up on his toes enough to fit their mouths together comfortably. He might be letting out breathy sighs but he can’t help it. He’s been waiting for Sam for hours longer than he originally anticipated and now that he finally has him, he want to kiss him silly. Actually, he can’t remember a time he wanted something this much because Sam feels strong and solid against him and he’s not even miffed that his little brother is holding on to him like he wouldn’t be able to stand without that help. That’s a little ridiculous because Dean’s got this, but he still doesn’t mind. It lets him lean into Sam more, fuck his tongue deeper and let Sam hold onto him as he coasts a hand down to give Sam’s ass a firm grab.

Sam flat out laughs, which is not the reaction Dean had been hoping for. Touching his lips for a moment before he licks them with interest. “You’ve been drinking.” He gets a curious gleam in his eyes and smirks. “ _What_ have you been up to, Dean? I thought you had work to do?”

Dean scowls at Sam for a second because he was expecting his brother to at least return the enthusiastic greeting. “Yeah, about that,” he hums with amusement. “You’ve got some work to do to catch up.” He turns with the slightest stumble, catches himself on the motel room’s table and holds himself upright so he can pour some whiskey in a second class. “Drink up Sammy,” he says as he offers his brother the glass.

Sam takes the glass but simply holds it in his hand as he studies his brother. “Dean?”

“ _Sam?”_ Dean mocks. Shaking his head, he steps forward, hooks his forefinger in the waist of Sam’s jeans and yanks him forward. The whiskey sloshes over the sides of the glass and Dean mourns its loss for a moment. He stops caring when he crashes his and Sam’s lips together again. This time, he hums happily as Sam returns the kiss with more fervor. The kiss gets dirty and soon they are nipping at each other’s lips and warring for dominance over the kiss.

Breaking away, Dean brings Sam’s hand and glass closer to his mouth. Trying to muster all the big brother prowess that he can, Dean lowers an eyebrow. “Come on, play along.” He helps tilt the glass against Sam’s lips and smirks as the man’s throat bobs to indicate that he’s swallowing. “That’a boy.” Once the brown liquid is drained, he tosses the glass on the floor and pitches forward, maybe with a little too much discoordination. A burst of laugher erupts from him before he captures Sam’s parted lips and licks the taste of whiskey out of his mouth. He keeps kissing Sam until all he can taste is his brother and only then does he take a step backwards. As much as he enjoys what they have going on, he has other plans for the two of them. “Come on.” Yanking Sam’s hand, he pulls the man towards a chair he set up at the opposite side of the room. Earlier, before the whiskey set in, he’d been quite calculated about this. There had been practice runs and measuring out paces. Now? Now, he’s just glad the damn chair is there because he gets to shove Sam into it with a little too much force.

“What the hell, Dean?” Sam cocks his head in confusion and runs a hand though his hair. He’s not pissed off but he definitely doesn’t like being kept in the dark.

“Just sit there.” Dean points a finger for good measure before spinning on his heels and walking to the other wall. He feels pretty smooth despite almost tripping once but he accredits that to the fact that his heart is pounding away in his chest due to the swirls of nervous excitement that are growing stronger. There was a bit of embarrassment thrown in there somewhere but he did a damn good job of drowning it out with lots of whiskey.

Dean flicks the light so that the only thing illuminating the room and Sam’s furrowed brows are the two bedside lamps. With another flail of his hand, he manages to push play on a room box he swiped from the main office. Being armed with a shoebox of cassette tapes left him with no other options. He’ll return it eventually.

Music floods the room, immediately loud and unavoidable.

It takes Sam a second to figure out what he’s listening to but when he does, he lets out a little amused snort. “Seriously? _Warrant_?” He laughs and raises both eyebrows in wait of an explanation from Dean.

On the defense, Dean rears back a bit and shakes his head at Sam. “Yeah, you got a problem with it? ‘Cherry Pie’ is a fucking stripper anthem and if you’ve got a problem with me trying to give you a striptease, then tell me now.” Dean has expected to just dive into it; voicing it makes him fumble over his words again and he supposes the nerves are still there.

Sam practically squeaks and his eyes go wider but he’s putting his hands up in surrender and shaking his head. “Nope, no problem.”

“Okay then.” Dean thinks he detects the hint of a smug expression on Sam’s face but he ignores it. “Sit down, shut up, and let me work here.” The song really starts, refrain a thing of the past, and Dean walks forward. He’s thankful he’s barefoot because he couldn’t think of a sexy way to kick off his boots. It allows him to drag his feet across the carpet in slow drawn out strides. He’s not a chick, despite the song’s pronouns, and he’s not about to start swinging his hips or anything, but he’s got slow and fluid down pat. The problem is, he’s feeling his blood alcohol level and it makes him sway inadvertently. Biting his lip, he starts to fumble with his flannel’s buttons. He gets a few of them undone while keeping up eye contact with Sam and tries to sync up each action to the thrum of the bass in the song.

Sam crosses his arms behind his head and runs his eyes over the lines of Dean’s body before he smirks. His eyes go back to Dean’s and he allows his older brother to trap him in a locked gaze.

By the time Dean gets his shirt unbuttoned, he’s much closer to Sam than he’d anticipated. It took a lot longer to get his shirt open than planned, so he hits the beat with a jut of his hips and tries to swing off the left shirt sleeve in one go. Problems arise when his arm gets snagged in it and he has to resort to tugging at it and flapping his arm around to dislodge the clothing. He tries to regain his composure, shoots Sam his most smoldering look, and attempts to strip out of the other sleeve. The same problem arises and he goes back to the very un-sexy flapping movements until he launches his shirt across the room. Growling in frustration, he pulls at the hem of the t-shirt he has underneath and yanks it over his head. Movement uncoordinated, he can’t figure out how to make tugging his head out of the shirt look enticing and kicks himself for not practicing more. The lack of having Sam as a focal point when he gets trapped in the cotton fabric makes him stumble once and have to widen his stance for balance. When he frees himself from the shirt, he tries to stand up proudly and give a sexy smirk but Sam’s dissolving into laughter.

“You’re really terrible at this,” Sam laughs through the hand loosely covering his mouth. His eyes are warm, however, and it’s obvious that he finds Dean’s attempt endearing.

“Shut up,” Dean barks and snorts. Determined to swing things into the right direction, he closes the gap between them and straddles Sam’s lap, rolling his hips clockwise as he takes a set on top of his younger brother. He rolls into Sam with the music and brings both hands to wrap around his neck so he can fit them more closely together. Grinding his hips down, he realizes Sam’s definitely giving him some attention down there. “I can’t be that bad at it if it has you hard already.”

“You’re basically dry humping me. Can you blame me?” Sam brings his hands up to slide along the strong muscles of Dean’s back and he sighs.

“ _I_ think I wasn’t that bad,” Dean says as he tilts his head and kisses Sam softly, teasing his bottom lip by grabbing it with his teeth and sucking it into his mouth. “Not done yet.”

That prompts an amused snort from Sam as he pulls the two of them together so they can deepen the kiss. Sam’s hands are big and strong on Dean’s form, forcing Dean exactly where Sam wants him.

They keep kissing but Dean doesn’t stop rolling into Sam in tune with the music. It keeps building up to the point where Dean feels exactly how hard he’s making Sam; leaving him all the more proud of his actions. His hips grind down with determination and Sam lets out a gasp. “Yeah, _definitely_ not that bad,” Dean says, voice gruff and heated. His words get muffled a bit as he can’t find a way to pull his lips away from Sam’s enough.

Sam growls possessively and rakes his hands down Dean’s sides, anchoring them around the curve of Dean’s hips and holding on. He keeps kissing Dean, occasionally rocking his hips up into the meat of Dean’s ass but as his thumbs hook inside Dean’s jeans, intent on rubbing over his older brother’s heated skin, he sucks in a surprised gasp.

The noise has Dean smirking and he figures that Sam’s just realized exactly why Dean’s not done. He feels warm and fuzzy and sits back enough to look at Sam with a drunk, happy smile on his face. Rolling his hips forward, he watches Sam’s hands yank his jeans’ button-fly open.

Sam’s hands go back to Dean’s sides where the denim is loose enough now for Sam to tug it down and try to expose the cut of Dean’s hips. His thumbs rub more firmly and they slip between layers of fabric to make contact with Dean’s skin before he slides both hands, palm down, around the back of Dean’s pants so he can cup is ass. There is a layer of fabric between them there but the gesture speaks of want. Licking his lips, Sam’s eyes are dark with lust. “Are you,” he pauses as if trying to realize the connotations of what he’s about to say. “Are you…wearing panties?”

“Well…figured it would be a helluva lot sexier than trying to shimmy out of a pair of boxer briefs.” Dean loses a bit of his cockiness there because…he’s wearing panties on his brother’s lap and he hadn’t been sure how that would turn out. Seems now that Sam’s discovered them, there’s not much to worry about. Still, the uncertainty he’d been feeling sneaks out for just a second before he can cover it up with a secure grin.

Sam bites his lower lip and groans. “Show me.”

“Was getting to that.” Dean tries to swing his leg over Sam and stand up but he’s more uncoordinated than he thought and he has to back off slowly to get to his own feet. The song is playing on loop, and Dean hopes he never has to explain to Sam why he even owns a copy of “Cherry Pie” that can play continuously for thirty minutes. Walking backwards, he starts to peel his jeans off, tugging them down an inch at a time until they are pooling at his legs and he gets caught up in them. He trips, falling backwards on his ass in a completely ungraceful fashion. Shaking his head to get himself back in the moment, Dean tries to free himself, leaving him nude except for a pair of lavender satin panties that are trying their hardest to contain his dick. They’re failing, actually, because the tip of Dean’s cock is peeking out the top after growing stiff from bumping and grinding with Sam.

Getting onto his knees and stretching his hands up towards the ceiling, Dean puts the power in his body on display. He notices the way Sam’s looking at him, fingers twitching with the need to touch. Even if he is doing a shitty job of giving a striptease, Dean’s succeeding in turning Sam on. He winks at Sam, the gesture feeling as cheesy as he hoped it wouldn’t but he forgets about it as he falls onto his hands and starts to crawl forward. In his head, this part was planned out. It was eight full crawls before he would hit Sam’s legs but he’s drunk. He can’t really ignore that fact any longer. And maybe, it’s for the best because he’s not sure he’d have the balls to do any of this without some liquid courage. The slow drag of his knees against the motel’s carpet isn’t as fluid as he wants but Dean manages to get closer to Sam. He’s sure he’s falling forward too heavily on his palms and maybe he’s oozing too much of his version of slutty, but he’s beyond caring. He tries to get to his feet but stumbles forward, spinning in the process and falls into an inverted V position. It leaves his ass in the air, facing Sam, and Dean starts laughing because Sam was right all along. He sucks at this.

“Christ, Dean…” Sam rumbles. The words, however, are so heavy with desire that they make Dean second guess his assessment of his actions. Sam’s on his feet immediately, hoisting Dean up and pressing him so that Dean’s naked back is pressed against Sam’s front. He immediately begins kissing the back of Dean’s neck and the spot behind his ear. His breathing is ragged and unsteady, evident with each slow drag of his lips across Dean’s skin. His jeans are tight and he’s rubbing against Dean so the man knows exactly how he feels about the situation at hand. “That was simultaneously the hottest and most pathetic thing I’ve ever seen.”

“You loved it,” Dean slurs out as he arches his neck so Sam can suck a bruise into it.

“I did.” Sam spins Dean and cups his jaw in his hands. “Fucking love _you_.”

“You big – ” The insult Dean has ready on his lips is swallowed down when Sam yanks him closer and kisses him roughly. Sam has a hand on each side of Dean’s face and he’s manipulating him so that he can’t break away. The kiss goes on for a while and just before Dean seriously thinks he’s going to need help standing upright if he can’t break away for enough air, Sam shoves Dean towards the bed.

Dean bounces on the mattress, propping himself on his elbows to see Sam lose all his clothing at record breaking speeds. Then he’s on top of Dean, bracketing his body with his arms and legs and hovering over him so that his hair falls in both of their faces. They’re kissing again and Dean lets out little moans when he feels Sam palming him through the satin of the panties.

“Where’d you get these panties” Sam gets out between kisses.

“Bought ‘em.” Dean smirks and rolls up into Sam’s erection. “Like ‘em?”

“You know damn well I do.” Sam laughs to himself as he palms Dean with a little more vigor. “God, I do. And…we’re so fucked up.” There is no self-pity in the words. They simply are what they are, like Sam’s okay with that.

“Speaking of fucked,” Dean adds with an eyebrow raise and an attempt to shift position. A firm hand to the center of his chest halts him completely and he blinks up at his younger brother.

“Oh no you don’t. You’re not going anywhere. You had your fun teasing me. Now it’s my turn.” Sam looks down Dean’s body. “Though, to be fair, I am probably not going to be doing much teasing. You got me too riled up already.” He leaves the bed for a split second but returns before Dean can actually move anywhere but further up the bed.

Dean smirks and lifts his hips so as to remove the panties but he’s stopped from doing so when Sam rolls him onto his belly and yanks his hips upward.

“Leave those on. I like the way they stretch over your ass. Wanna see how wet and messy they get after I’m through with you.” Sam smacks Dean’s ass once before cupping each globe in a hand and squeezing. He leans down to kiss the satin covered area, dragging his lips across it and the fabric darkens just slightly with saliva.

Dean moans into the pillow his head has found itself on and braces his weight on his forearms. He hears the snick of a cap and knows Sam’s got their lube. It makes him shiver in anticipation because that sound always comes with good things. Even though he knows what’s coming, he gasps when Sam yanks the panties to the side enough so that he can run a slick finger over the furled muscle between Dean’s ass cheeks.

Sam’s buzzing with exhilaration; it’s practically palpable. He keeps making noises of enjoyment as he teases at Dean’s opening and pushes one finger inside. He takes his time in exploring the area, curling his finger and pressing it along all sides of the rim. Dean’s moaning in time with his touches and Sam gives in, adding another finger and coaxing more moans out of Dean.

Dean closes his eyes and he’s fucking floating. The buzz he’d had has left him in a place where everything is _good_. He can feel the way Sam is working him open, taking his time, and even though Sam said he probably wouldn’t tease, that’s what he is doing anyway. Dean would have been begging for Sam’s dick if his mouth felt like working. But, as is, he can’t do more than whimper, groan, and let out breathy sighs of pleasure.

By the time Sam gets three fingers inside, his little brother sounds wrecked. He leans back to sit on his heels and observes the way Dean’s taking his fingers and how the panties keep slipping in the way. The fabric there is damp with lube and Dean knows the front isn’t doing much better because his dick’s been weeping from the first time Sam had one finger deep inside of him and moaned so prettily.

“Fuck, you look so good, Dean.” Sam hisses and bites his lip.

“Feel good too,” Dean manages to get out but he whines when Sam’s fingers leave him feeling empty.

“Give me a second,” Sam says as he squeezes a dollop of lube into his palm and slicks up his own arousal. “We’re still keeping these on,” he reminds as he gets into position and guides his dick to press against Dean’s opening.

Dean’s impatient, like he always is. He shifts his hips backwards and steals the pleasure of having control away from Sam. Even though the move is a bit sloppy, he gets Sam where he wants him; sheathed deep inside his body. It is a solid movement that leaves both men gasping.

After that, Dean stops caring who is controlling what. He fists the bed sheets and keeps himself firmly positioned so that he can take the thrusting he’s hoping Sam will give him.

He’s not disappointed when Sam starts moving his hips. Everything dissolves into sweaty, slippery movements and the feeling of Sam’s cockhead brushing up against his prostate. Sam’s panting in his ears and Dean purrs, relaxing himself to take as much of his brother as he can.

Sam’s hands fall to Dean’s hips and he holds on tight enough to leave bruises in the morning. He’s pistoning his hips, feeding Dean every inch of arousal that twitched to life during the striptease.

“Cherry Pie” is still blaring in their ears. For a second, Dean catches the lyrics. He laughs because he’s thinking that he doesn’t want this to end quite yet, and thinking about baseball might be a great tactic if he wants to starve off his orgasm a while longer.

It’s impossible because Sam overrides all thoughts of baseball. Nothing could dampen Dean’s arousal when he’s got Sam pounding into him like that and Sam seals the deal by snaking a hand around Dean and slipping it into the panties so he can fist him. Dean cries out; Sam gives a proud snort.

They move like that for a while, until Sam’s getting wilder. His thrusts aren’t as composed and planned out and he’s shivering enough to let Dean know he’s close. Really close.

“Fuck, Dean….gonna…gonna come all over you. Inside you…on you…”

Dean’s not really sure what he means but the way his voice sounds pitches Dean over the edge. He’s glad Sam had spent the time teasing him because it makes his orgasm all the better. With a gap, Dean falls forward on his forearms more and comes. “Sam!” He lets everything race through him as his dick pulses and covers Sam’s fist, the panties, the bed, anything within spattering distance. His brain is far away but he’s aware enough that Sam’s letting out strangled moans. He feels the way Sam tenses like he always does before coming and Dean gives a goofy grin as he feels his brother start to shoot off inside him. There is warmth there and he’s become accustomed to feeling it and feeling satisfaction in it.

Then Sam pulls back and out of Dean, his cock still spilling strings of come as Sam takes over Dean’s job and starts jacking his dick with a messy fist. The come lands on Dean’s spent hole as well as the bunched up panties he’s still wearing. It must do something amazing to Sam’s brain because he’s singing Dean’s name like a litany.

When Sam slumps forward, blanketing Dean’s form but careful enough not to crush him, they both are frozen in the moment. The silence isn’t uncomfortable and Dean’s left to think on what just happened. He can feel Sam’s come dripping out of him and knows, without having to look, that Sam made quite a mess of him.

“Heavy,” Dean complains and elbows Sam enough so that he gets the point and rolls to the side. It allows Dean the chance to roll on his back. Chest heaving, he tries to catch his breath.

“Fuck,” Sam breaths out on something that sounds like a laugh and sound of awe. “Look at you.” Even though he just came, Sam bits his lips like he can’t handle how enticing what he’s looking at is.

Dean looks and notices that Sam was right. The panties are completely decimated by wet marks and come. They look about as debauched as anything Dean’s ever seen. “Nice work,” Dean says in amusement, but he’s exhausted and the words slur.

Sam rolls onto his side so he can kiss the underside of Dean’s chin and work his way up. It’s sweet and slow, practically the opposite of what they just did. “I don’t know what got into you tonight…but…I think we should keep the panties. I…I like them.”

“Yeah?”

“Yeah,” Sam says with a soft kiss to Dean’s lips. “Thank you.”

“I didn’t do all this for you,” Dean adds. But he did and they both know it. Still, he can’t help but realize that maybe he needed this break as much as Sam did. “Though, I kinda liked it too.”

“You gotta work on your striptease technique.”

Dean elbows Sam in the ribs but he laughs. “Oh, yeah? Maybe you should show me how it’s done, huh?” Dean can feel Sam’s smile against his neck as his brother pulls him closer.

“Maybe I should.” Yawning, Sam manages to slot his leg between Dean’s and fit them together.

Dean rolls his eyes. Sam’s lucky Dean’s drunk because he doesn’t have the energy to swat Sam’s limbs away. It’s a constant battle between the two of them and Dean has no idea how Sam can sleep with their legs and arms tangled around each other. Sam swears it’s comforting but all Dean feels is trapped because once Sam’s asleep, Dean doesn’t dare move. It’s a stupid trait he picked up years ago but he’s always afraid he’ll disturb his brother so he habitually puts Sam’s comfort before his own. Now, he knows he’ll pass out before Sam. There’s no harm in slipping into unconsciousness as a mess of Winchester appendages. And Sam’s kissing his neck and nuzzling into him. It feels kind of nice.

When he’s awake and sober, he’s going to hold Sam to that statement.

He falls asleep to thoughts of Sam giving the striptease of a lifetime and what it is like to fuck him after that.

It’s a good dream.

**Works inspired by this one:**

  * [ART: Lavender panties](https://archiveofourown.org/works/2303615) by [kjanddean](https://archiveofourown.org/users/kjanddean/pseuds/kjanddean)




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